An in person meet (even if you have to drive 4 hours) would be the best way.

And I do have the photos at the end by design, because I want a person to end the experience with a specific feeling of "oh wow, look at that, it's got that too", which helps drive conversion. 

It takes me 10~ minutes to get on Lake Shore drive, then it's pretty easy to navigate the city. 

If you're local, you can start by really learning the market by driving the neighborhoods, studying recent sales, and getting to know what areas investors are targeting.

GO DRIVE A TRUCK IRL.

You cannot get any meaningful answers until you specify what is your "side gig", how much money it's going to bring and how much expenses it's going to incur, and what kind of expenses.And, as a rule of thumb, unless you clear $50k after all expenses, you probably will not benefit from any entities tax-wise. 

Last night, I heard an inspiring story about a mom who brought her young kids along for a 45-minute drive to tour an investment property.

Drive around and figure out a few areas you would like to live in with your budget.

The property has 7 acres with a 3/2 main house and a second separate 2/1 house (which also needs renovation) with its own drive.  

This influx of workers will naturally drive demand for housing, retail, and other services in the surrounding areas, especially in smaller towns and cities that haven't seen major growth in decades.